PL234826B1 - Method for obtaining a mixture of 3'-O-β-D-glucopyranosyl-5,7-dihydroxy-4'-methoxyflavanone and 7-O-β-D-glucopyranosyl-3',5-dihydroxy-4'-methoxyflavanone - Google Patents
Method for obtaining a mixture of 3'-O-β-D-glucopyranosyl-5,7-dihydroxy-4'-methoxyflavanone and 7-O-β-D-glucopyranosyl-3',5-dihydroxy-4'-methoxyflavanone Download PDFInfo
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- glucopyranosyl
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- methoxyflavanone
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- 238000000034 method Methods 0.000 title claims abstract description 16
- 239000000203 mixture Substances 0.000 title claims abstract description 13
- 241000293029 Absidia caerulea Species 0.000 claims abstract description 12
- 230000009466 transformation Effects 0.000 claims abstract description 11
- 239000000758 substrate Substances 0.000 claims abstract description 8
- AIONOLUJZLIMTK-AWEZNQCLSA-N hesperetin Chemical compound C1=C(O)C(OC)=CC=C1[C@H]1OC2=CC(O)=CC(O)=C2C(=O)C1 AIONOLUJZLIMTK-AWEZNQCLSA-N 0.000 claims abstract description 4
- 241000233866 Fungi Species 0.000 claims description 4
- 230000000813 microbial effect Effects 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 238000004587 chromatography analysis Methods 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- 239000003153 chemical reaction reagent Substances 0.000 claims description 2
- 239000012043 crude product Substances 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 239000000047 product Substances 0.000 claims description 2
- 238000003756 stirring Methods 0.000 claims description 2
- 235000001674 Agaricus brunnescens Nutrition 0.000 claims 1
- 235000013305 food Nutrition 0.000 abstract description 3
- 230000002906 microbiologic effect Effects 0.000 abstract description 3
- 150000001875 compounds Chemical class 0.000 abstract description 2
- 230000002255 enzymatic effect Effects 0.000 abstract 1
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 108090000790 Enzymes Proteins 0.000 description 2
- 102000004190 Enzymes Human genes 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 229930003935 flavonoid Natural products 0.000 description 2
- 235000017173 flavonoids Nutrition 0.000 description 2
- 239000001100 (2S)-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)chroman-4-one Substances 0.000 description 1
- 241000282461 Canis lupus Species 0.000 description 1
- 241000207199 Citrus Species 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 244000017020 Ipomoea batatas Species 0.000 description 1
- 235000002678 Ipomoea batatas Nutrition 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 244000061456 Solanum tuberosum Species 0.000 description 1
- 235000002595 Solanum tuberosum Nutrition 0.000 description 1
- 230000001028 anti-proliverative effect Effects 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000036983 biotransformation Effects 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 238000004113 cell culture Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 235000020971 citrus fruits Nutrition 0.000 description 1
- 239000000287 crude extract Substances 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- -1 flavonoid compounds Chemical class 0.000 description 1
- 150000002215 flavonoids Chemical class 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 230000013595 glycosylation Effects 0.000 description 1
- 238000006206 glycosylation reaction Methods 0.000 description 1
- AIONOLUJZLIMTK-UHFFFAOYSA-N hesperetin Natural products C1=C(O)C(OC)=CC=C1C1OC2=CC(O)=CC(O)=C2C(=O)C1 AIONOLUJZLIMTK-UHFFFAOYSA-N 0.000 description 1
- 235000010209 hesperetin Nutrition 0.000 description 1
- 229960001587 hesperetin Drugs 0.000 description 1
- FTODBIPDTXRIGS-UHFFFAOYSA-N homoeriodictyol Natural products C1=C(O)C(OC)=CC(C2OC3=CC(O)=CC(O)=C3C(=O)C2)=C1 FTODBIPDTXRIGS-UHFFFAOYSA-N 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000004114 suspension culture Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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- Pyrane Compounds (AREA)
- Saccharide Compounds (AREA)
Abstract
Zgłoszenie dotyczy sposobu otrzymywania mieszaniny 3'-O-ß-D-glukopiranozylo-5,7-dihydroksy-4'-metoksyflawanonu, o wzorze 2 i 7-O-ß-D-glukopiranozylo-3',5-dihydroksy-4'-metoksyflawanonu, o wzorze 3, na drodze transformacji mikrobiologicznej, przy użyciu systemu enzymatycznego grzybów z gatunku Absidia coerulea. Jako substrat stosuje się 3',5,7-trihydroksy-4'-metoksyflawanon o wzorze 1. Związki będące przedmiotem zgłoszenia, są biologicznie czynne i mogą mieć zastosowanie w przemyśle spożywczym i farmaceutycznym.The application concerns a method for obtaining a mixture of 3'-O-ß-D-glucopyranosyl-5,7-dihydroxy-4'-methoxyflavanone, formula 2, and 7-O-ß-D-glucopyranosyl-3',5-dihydroxy-4' -methoxyflavanone, of formula 3, by microbiological transformation, using the enzymatic system of Absidia coerulea fungi. 3',5,7-trihydroxy-4'-methoxyflavanone of formula 1 is used as the substrate. The compounds subject to the application are biologically active and may be used in the food and pharmaceutical industries.
Description
Opis wynalazkuDescription of the invention
Przedmiotem wynalazku jest sposób otrzymywania mieszaniny 3'-0-^-D-glukopiranozylo-5,7-dihydroksy-4'-metoksyflawanonu o wzorze 2 i 7-0-^-D-glukopiranozylo-3',5-dihydroksy-4'-metoksyflawanonu o wzorze 3 przedstawionych na rysunku.The subject of the invention is a process for the preparation of a mixture of 3'-O - N-D-glucopyranosyl-5,7-dihydroxy-4'-methoxyflavanone of the formula 2 and 7-0 - ^ - D-glucopyranosyl-3 ', 5-dihydroxy-4' -methoxyflavanone of the formula 3 shown in the figure.
Budowa chemiczna otrzymanych składników mieszaniny wskazuje na ich aktywność biologiczną oraz ich potencjalne zastosowanie w przemyśle spożywczym i farmaceutycznym. W literaturze opisano aktywność przeciwnowotworową 7-0-^-D-glukopiranozylo-3',5-dihydroksy-4'-metoksyflawanonu [J.A. Manthey, N. Guthrie: „Antiproliferative activities of citrus flavonoids against six human cancer cell lines”, J. Agric. Food Chem., 2002, 50, 5837-5843].The chemical structure of the obtained components of the mixture indicates their biological activity and their potential use in the food and pharmaceutical industries. The anti-tumor activity of 7-O - 1 - D-glucopyranosyl-3 ', 5-dihydroxy-4'-methoxy flavanone has been described in the literature [J.A. Manthey, N. Guthrie: "Antiproliferative activities of citrus flavonoids against six human cancer cell lines", J. Agric. Food Chem., 2002, 50, 5837-5843].
W literaturze znana jest metoda otrzymywania 3'-0-^-D-glukopiranozylo-5,7-dihydroksy-4'-metoksyflawanonu i 7-0-^-D-glukopiranozylo-3',5-dihydroksy-4'-metoksyflawanonu w zawiesinowej kulturze komórek wilca ziemniaczanego (Ipomoea batatas) [K. Shimoda, H. Hamada, H. Hamada: „Glycosylation of hesperetin by plant cell cultures”, Phytochemistry, 2007, 69, 1135-1140].There is known in the literature the method of obtaining 3'-O - ^ - D-glucopyranosyl-5,7-dihydroxy-4'-methoxy flavanone and 7-0 - ^ - D-glucopyranosyl-3 ', 5-dihydroxy-4'-methoxy flavanone in the suspension culture of potato wolf (Ipomoea batatas) cells [K. Shimoda, H. Hamada, H. Hamada: "Glycosylation of hesperetin by plant cell cultures", Phytochemistry, 2007, 69, 1135-1140].
Nie jest znana natomiast metoda otrzymywania tej mieszaniny na drodze transformacji mikrobiologicznej.However, the method of obtaining this mixture by microbiological transformation is not known.
Szczep Absidia coerulea AM 93 zdeponowany jest w kolekcji mikroorganizmów Katedry Chemii Uniwersytetu Przyrodniczego we Wrocławiu (ul. C K. Norwida 25, 50-375 Wrocław).Absidia coerulea AM 93 strain is deposited in the collection of microorganisms of the Department of Chemistry, University of Life Sciences in Wrocław (C K. Norwida 25, 50-375 Wrocław).
Znane są procesy biotransformacji przy udziale grzybów strzępkowych z gatunku Absidia coerulea. Opisano m. in. jego zdolność do glikozylacji związków flawonoidowych. W wyniku działania układu enzymatycznego zawartego w żywych komórkach kultury Absidia coerulea otrzymano szereg związków. Z opisu patentowego PL 223 441 znana jest metoda otrzymywania 4'-O-3-D-glukopiranozylo-4,2'-dihydroksy-6'-metoksy-3'-prenylo-a,3-dihydrochalkonu, z opisu PL 226315 znany jest sposób otrzymywania 2'-O-3-D-glukopiranozylo-1'',2,a,3-tetrahydroksantohumolu C, z PL 223446 - 4'-O-3-D-glukopiranozyloksantohumolu C, opis PL 222175 ujawnia otrzymywanie 4'-O-3-D-glukopiranozylo-3-[1'-hydroksyizopropylo]-4,2'-dihydroksy-6'-metoksy-3'-prenylo-a,3-dihydrochalkonu, opis PL 222731 wskazuje na otrzymywanie mieszaniny 7-O-3-D-glukopiranozylo-5-hydroksy-4'-metoksyizoflawonu i 5-O-3-D-glukopiranozylo-7-hydroksy-4'-metoksyizoflawonu, natomiast PL 219084 opisuje otrzymywanie 4'-O-3-D-glukozylo-2',4-dihydroksy-6’-metoksy-3'-prenylochalkonu.Biotransformation processes involving filamentous fungi of the Absidia coerulea species are known. Among other things, its ability to glycosylate flavonoid compounds. As a result of the action of the enzyme system contained in living cells of Absidia coerulea culture, a number of compounds were obtained. The method of obtaining 4'-O-3-D-glucopyranosyl-4,2'-dihydroxy-6'-methoxy-3'-prenyl-a, 3-dihydroochalcone is known from the patent description PL 223 441, from the description PL 226315 it is known method for the preparation of 2'-O-3-D-glucopyranosyl-1 ", 2, a, 3-tetrahydroxanthohumol C, from PL 223446 - 4'-O-3-D-glucopyranosylxanthohumol C, description PL 222175 discloses the preparation of 4'- O-3-D-glucopyranosyl-3- [1'-hydroxyisopropyl] -4,2'-dihydroxy-6'-methoxy-3'-prenyl-a, 3-dihydroochalcone, the description of PL 222731 indicates the preparation of a 7-O mixture -3-D-glucopyranosyl-5-hydroxy-4'-methoxyisoflavone and 5-O-3-D-glucopyranosyl-7-hydroxy-4'-methoxyisoflavone, while PL 219084 describes the preparation of 4'-O-3-D-glucosyl -2 ', 4-dihydroxy-6'-methoxy-3'-prenylchalcone.
Istotą wynalazku jest sposób otrzymywania mieszaniny 3'-0-^-D-glukopiranozylo-5,7-dihydroksy-4'-metoksyflawanonu i 7-0-^-D-glukopiranozylo-3',5-dihydroksy-4'-metoksyflawanonu, polegający na tym, że substrat, którym jest 3',5,7-trihydroksy-4'-metoksyflawanon, poddaje się transformacji mikrobiologicznej, w wyniku czego otrzymuje się mieszaninę 3'-0-^-D-glukopiranozylo-5,7-dihydroksy-4’-metoksyflawanonu i 7-0-^-D-glukopiranozylo-3',5-dihydroksy-4'-metoksyflawanonu. Grzyby strzępkowe z gatunku Absidia coerulea namnaża się w płynnym podłożu mikrobiologicznym, przy ciągłym mieszaniu reagentów, w temperaturze 12-40°C. Następnie do narośniętej hodowli dodaje się substrat i dalej prowadzi proces, aż do całkowitego zużycia substratu. Po zakończeniu transformacji roztwór transformacyjny, ekstrahuje się rozpuszczalnikiem organicznym niemieszającym się z wodą, oddziela frakcję organiczną, osusza bezwodnym siarczanem magnezu, odparowuje rozpuszczalnik i tak otrzyman y surowy produkt oczyszcza się za pomocą technik chromatograficznych.The essence of the invention is the method of obtaining a mixture of 3'-O - ^ - D-glucopyranosyl-5,7-dihydroxy-4'-methoxy flavanone and 7-0 - ^ - D-glucopyranosyl-3 ', 5-dihydroxy-4'-methoxy flavanone, in which the substrate 3 ', 5,7-trihydroxy-4'-methoxyflavanone is subjected to a microbiological transformation to obtain a mixture of 3'-O - ^ - D-glucopyranosyl-5,7-dihydroxy -4'-methoxy flavanone and 7-O - N - D-glucopyranosyl-3 ', 5-dihydroxy-4'-methoxy flavanone. Filamentous fungi of the species Absidia coerulea are multiplied in a liquid microbial medium under constant stirring of the reagents at a temperature of 12-40 ° C. Subsequently, a substrate is added to the grown culture and the process is continued until the substrate is completely consumed. After completion of the transformation, the transformation solution is extracted with a water-immiscible organic solvent, the organic fraction is separated, dried over anhydrous magnesium sulfate, the solvent is evaporated, and the crude product thus obtained is purified by chromatographic techniques.
Korzystnie także jest, gdy transformację prowadzi się szczepem Absidia coerulea AM 93.It is also preferred that the transformation is carried out with the strain Absidia coerulea AM 93.
Korzystnie jest, gdy reakcję prowadzi się w temperaturze 26°C.It is advantageous when the reaction is carried out at a temperature of 26 ° C.
Postępując zgodnie z wynalazkiem, w wyniku działania układu enzymatycznego zawartego w żywych komórkach kultury Absidia coerulea następuje reakcja glukozylacji substratu.In accordance with the invention, the substrate glucosylation is reacted by the action of the enzyme system contained in the living cells of Absidia coerulea.
Zasadniczą zaletą wynalazku jest otrzymanie, w łagodnych warunkach mieszaniny 3'-0-/>-D-glukopiranozylo-5,7-dihydroksy-4'-metoksyflawanonu i 7-0-^-D-glukopiranozylo-3',5-dihydroksy-4'-metoksyflawanonu, jako głównych produktów reakcji w kulturze Absidia coerulea. Wydajność reakcji dla 3'-0-^-D-glukopiranozylo-5,7-dihydroksy-4'-metoksyflawanonu osiąga poziom ponad 5%, zaś dla 7-0-^-D-glukopiranozylo-3',5-dihydroksy-4'-metoksyflawanonu 35%.The main advantage of the invention is the preparation, under mild conditions, of a mixture of 3'-O-> - D-glucopyranosyl-5,7-dihydroxy-4'-methoxyflavanone and 7-0 - ^ - D-glucopyranosyl-3 ', 5-dihydroxy- 4'-methoxyflavanone as the main reaction products in Absidia coerulea culture. The reaction yield for 3'-0 - ^ - D-glucopyranosyl-5,7-dihydroxy-4'-methoxyflavanone is over 5%, and for 7-0 - ^ - D-glucopyranosyl-3 ', 5-dihydroxy-4 β-methoxyflavanone 35%.
Wynalazek jest bliżej objaśniony w przykładzie wykonania.The invention is explained in more detail in an embodiment.
P r z y k ł a d 1. Do kolby o pojemności 300 cm3, w której znajduje się 100 cm3 sterylnej pożywki zawierającej 3 g glukozy i 1 g aminobaku na 1 dm3 wody destylowanej, wprowadza się grzyby strzępkowe Absidia coerulea AM 93. Po 6 dniach wzrostu drobnoustrojów w temperaturze 26°C i przy ciągłym wstrząsaniu, dodaje się 15 mg 3',5,7-trihydroksy-4'-metoksyflawanonu, o wzorze 1, rozpuszczonego w 1,5 cm3 dimetylosulfotlenku. Transformację prowadzi się przy ciągłym wstrząsaniu przez 10 dób. PoEXAMPLE 1 To a flask of 300 cm 3, which is 100 cm 3 of sterile medium containing 3 g of glucose and 1 g aminobaku per 1 dm 3 of distilled water is introduced into filamentous fungus Absidia coerulea AM 93. After 6 days, microbial growth at 26 ° C with continuous shaking, is added 15 mg of 3 ', 5,7-trihydroxy-4'-metoksyflawanonu of formula 1, dissolved in 1.5 cm 3 of dimethyl sulfoxide. The transformation is carried out under continuous shaking for 10 days. After
PL 234 826 B1 tym czasie hodowlę zakwasza się 1-molowym kwasem chlorowodorowym do pH 4,5. Następnie, uzyskany roztwór transformacyjny ekstrahuje się trzykrotnie octanem etylu, osusza bezwodnym siarczanem magnezu i odparowuje rozpuszczalnik. Uzyskuje się 12,5 mg surowego ekstraktu, który oczyszcza się chromatograficznie, używając jako eluentu mieszaninę chloroform : metanol w stosunku objętościowym 7:1. Po oczyszczeniu otrzymuje się 9,5 mg mieszaniny 3’-0-^-D-glukopiranozylo-5,7-dihydroksy-4'-metoksyflawanonu, o wzorze 2 i 7-0-^-D-glukopiranozylo-3',5-dihydroksy-4'-metoksyflawanonu, o wzorze 3 z wydajnością 5,6% dla 3'-0-^-D-glukopiranozylo-5,7-dihydroksy-4'-metoksyflawanonu i 35,5% dla 7-0-^-D-glukopiranozylo-3',5-dihydroksy-4'-metoksyflawanonu.At this time, the culture is acidified with 1 M hydrochloric acid to a pH of 4.5. Then, the resulting transformation solution was extracted three times with ethyl acetate, dried with anhydrous magnesium sulfate, and the solvent was evaporated. This yields 12.5 mg of crude extract which is purified by chromatography using 7: 1 by volume chloroform: methanol as eluent. After purification, 9.5 mg of a mixture of 3'-O - N-D-glucopyranosyl-5,7-dihydroxy-4'-methoxy flavanone of the formula 2 and 7-O - N -D-glucopyranosyl-3 ', 5- dihydroxy-4'-methoxy flavanone, of formula 3 in 5.6% yield for 3'-O - ^ - D-glucopyranosyl-5,7-dihydroxy-4'-methoxy flavanone and 35.5% for 7-0 - ^ - D-glucopyranosyl-3 ', 5-dihydroxy-4'-methoxy flavanone.
Uzyskane produkty charakteryzują się następującymi danymi spektralnymi: 3'-0-^-D-glukopiranozylo-5,7-dihydroksy-4'-metoksyflawanon: 1H NMR (600 MHz, DMSO-d6) δ (ppm): 2,70 (1H, dd, J=3,2; 17,1 Hz, H-3eq), 3,14 (1H, t, J=9,4 Hz, H-4), 3,25-3,28 (1H, m, H-2), 3,24-3,41 (2H, m, H-3, H-5), 3,27 (1H, m, H-3ax), 3,40-3,47 (1H, m, Ha-6), 3,64-3,67 (1H, m, Hb-6''), 3,77 (3H, s, 4'OCHs) 4,95 (1H, d, J=7,6 Hz, H-1), 5,45 (1H, dd, J=3,2; 12,3 Hz, H-2), 5,88 (1H, d, J=2,1 Hz, H-6), 5,90 (1H, d, J=2,1 Hz, H-8a), 5,91 (1H, d, J=2,1 Hz, H-8b), 7,00 (1H, d, J=8,4 Hz, H-5'a), 7,01 (1H, d, J=8,4 Hz, H-5'b), 7,07 (1H, dd, J=2,1; 8,4 Hz, H-6'a), 7,08 (1H, dd, J=2,1; 8,4 Hz, H-6'b), 7,23 (1H, d, J=2,1 Hz, H-2'), 13C NMR (150 MHz, DMSO-d6) δ (ppm): 41,95 (C-3a), 42,04 (C-3b), 55,74 (4'OCHsa), 55,77 (4'OCH3b),60,59 (C-6), 69,71 (C-4) 73,16 (C-2”), 76,34 (C-3), 77,02 (C-5), 78,47 (C-2), 95,09 (C-8), 95,49 (C-6), 99,68 (C-1''a), 99,96 (C-1''b), 101,75 (C-10), 112,20 (C-5'), 113,79 (C-2'), 120,35 (C-6'a), 120,60 (C-6'b), 130,89 (C-1'a), 130,91 (C-1'a), 146,30 (C-3'), 149,14 (C-4'), 162,92 (C-9a), 162,94 (C-9b), 163,49 (C-5), 166,80 (C-7), 196,28 (C-4).The resulting products are characterized by the following spectral data: 3'-0 - ^ - D-glucopyranosyl-5,7-dihydroxy-4'-methoxyflavanone: 1 H NMR (600 MHz, DMSO-d6) δ (ppm): 2.70 ( 1H, dd, J = 3.2; 17.1 Hz, H-3eq), 3.14 (1H, t, J = 9.4 Hz, H-4), 3.25-3.28 (1H, m, H-2), 3.24-3.41 (2H, m, H-3, H-5), 3.27 (1H, m, H-3ax), 3.40-3.47 (1H , m, Ha-6), 3.64-3.67 (1H, m, Hb-6 "), 3.77 (3H, s, 4'OCHs) 4.95 (1H, d, J = 7 , 6 Hz, H-1), 5.45 (1H, dd, J = 3.2; 12.3 Hz, H-2), 5.88 (1H, d, J = 2.1 Hz, H- 6), 5.90 (1H, d, J = 2.1Hz, H-8a), 5.91 (1H, d, J = 2.1Hz, H-8b), 7.00 (1H, d , J = 8.4 Hz, H-5'a), 7.01 (1H, d, J = 8.4 Hz, H-5'b), 7.07 (1H, dd, J = 2.1 ; 8.4 Hz, H-6'a), 7.08 (1H, dd, J = 2.1; 8.4 Hz, H-6'b), 7.23 (1H, d, J = 2 , 1 Hz, H-2 '), 13 C NMR (150 MHz, DMSO-d6) δ (ppm): 41.95 (C-3a), 42.04 (C-3b), 55.74 (4' OCH), 55.77 (b 4'OCH 3), 60.59 (C-6), 69.71 (C-4), 73.16 (C-2 '), 76.34 (C-3), 77.02 (C-5), 78.47 (C-2), 95.09 (C-8), 95.49 (C-6), 99.68 (C-1 '), 99, 96 (C-1''b), 101.75 (C-10), 112.20 (C-5 '), 113.79 (C-2'), 120.35 (C-6'a), 1 20.60 (C-6'b), 130.89 (C-1'a), 130.91 (C-1'a), 146.30 (C-3 '), 149.14 (C-4 '), 162.92 (C-9a), 162.94 (C-9b), 163.49 (C-5), 166.80 (C-7), 196.28 (C-4).
7-0-^-D-glukopiranozylo-3',5-dihydroksy-4'-metoksyflawanon 1H NMR (600 MHz, DMSO-d6) δ (ppm): 2,75 (1H, dd, J=3,2; 17,1 Hz, H-3aeq), 2,77 (1H, dd, J=3,2; 17,1 Hz, H-3beq), 3,14 (1H, t, 3=9,4 Hz, H-4''), 3,20 (1H, m, H-2''), 3,24-3,41 (2H, m, H-3'', H-5''), 3,27 (1H, m, H-3ax), 3,40-3,47 (1H, m, Ha-6''), 3,64-3,67 (1H, m, Hb-6''), 3,77 (3H, s, 4'OCHs) 4,96 (1H, d, J=7,7 Hz, H-1''a), 4,98 (1H, d, 3=7,7, H-1b), 5,48 (1H, dd, J=3,2; 12,3 Hz, H-2a), 5,49 (1H, dd, J=3,2; 12,3 Hz, H-2b), 6,13 (1H, d, J=2,1 Hz, H-6a), 6,14 (1H, d, J=2,1 Hz, H-6b), 6,15 (1H, d, J=2,1 Hz, H-8a), 6,16 (1H, d, J=2,1 Hz, H-8b), 6,88 (1H, m, H-6'), 6,94 (2H, m, H-2', H-5'), 13C NMR (150 MHz, DMSO-d6) δ (ppm): 42,16 (C-3), 55,70 (4'OCH3), 60,59 (C-6), 69,51 (C-4), 73,03 (C-2''), 76,34 (C-3''), 77,09 (C-5), 78,50 (C-2a), 78,54 (C-2b), 95,86 (C-8), 96,50 (C-6), 99,47 (C-1a), 99,59 (C-1b), 103,30 (C-10), 112,00 (C-5'), 114,17 (C-2'), 117,85 (C-6'), 130,85 (C-1'), 146,49 (C-3'), 147,99 (C-4'a), 148,00 (C-4'b), 162,62 (C-9a), 162,66 (C-9b), 162,86 (C-5), 165,23 (C-7a), 165,31 (C-7b), 197,10 (C-4).7-0 - ^ - D-glucopyranosyl-3 ', 5-dihydroxy-4'-methoxyflavanone 1 H NMR (600 MHz, DMSO-d6) δ (ppm): 2.75 (1H, dd, J = 3.2 ; 17.1 Hz, H-3aeq), 2.77 (1H, dd, J = 3.2; 17.1 Hz, H-3beq), 3.14 (1H, t, 3 = 9.4 Hz, H-4 "), 3.20 (1H, m, H-2"), 3.24-3.41 (2H, m, H-3 ", H-5"), 3.27 (1H, m, H-3ax), 3.40-3.47 (1H, m, Hb-6 "), 3.64-3.67 (1H, m, Hb-6"), 3, 77 (3H, s, 4'OCHs) 4.96 (1H, d, J = 7.7Hz, H-1''s), 4.98 (1H, d, 3 = 7.7, H-1b ), 5.48 (1H, dd, J = 3.2; 12.3 Hz, H-2a), 5.49 (1H, dd, J = 3.2; 12.3 Hz, H-2b), 6.13 (1H, d, J = 2.1Hz, H-6a), 6.14 (1H, d, J = 2.1Hz, H-6b), 6.15 (1H, d, J = 2.1Hz, H-8a), 6.16 (1H, d, J = 2.1Hz, H-8b), 6.88 (1H, m, H-6 '), 6.94 (2H, m, H-2 ', H-5'), 13 C NMR (150 MHz, DMSO-d6) δ (ppm): 42.16 (C-3), 55.70 (4'OCH 3 ), 60, 59 (C-6), 69.51 (C-4), 73.03 (C-2 "), 76.34 (C-3"), 77.09 (C-5), 78.50 (C-2a), 78.54 (C-2b), 95.86 (C-8), 96.50 (C-6), 99.47 (C-1a), 99.59 (C-1b) , 103.30 (C-10), 112.00 (C-5 '), 114.17 (C-2'), 117.85 (C-6 '), 130.85 (C-1'), 146.49 (C-3 '), 147.99 (C-4'a), 148.00 (C-4'b), 162.62 (C-9a), 162.66 (C-9b), 162.86 (C-5), 165.23 (C-7a), 165.31 (C-7b), 197.10 (C-4) .
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| WO2016012198A1 (en) * | 2014-07-01 | 2016-01-28 | Symrise Ag | Method for the biotechnological production of flavone glycoside dihydrochalcones |
| PL222731B1 (en) * | 2014-03-28 | 2016-08-31 | Univ Przyrodniczy We Wrocławiu | Method of obtaining 7-O--D-glucopyranosyl-5-hydroxy-4'-methoxyisoflavone and 5-O--D-glucopyranosyl-7-hydroxy-4'-methoxyisoflavone |
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| PL222731B1 (en) * | 2014-03-28 | 2016-08-31 | Univ Przyrodniczy We Wrocławiu | Method of obtaining 7-O--D-glucopyranosyl-5-hydroxy-4'-methoxyisoflavone and 5-O--D-glucopyranosyl-7-hydroxy-4'-methoxyisoflavone |
| WO2016012198A1 (en) * | 2014-07-01 | 2016-01-28 | Symrise Ag | Method for the biotechnological production of flavone glycoside dihydrochalcones |
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| KEI SHIMODA ET AL: "2008", "GLYCOSYLATION OF HESPERETIN BY PLANT CELL CULTURES" * |
| KEI SHIMODA ET AL: "2010", "PRODUCTION OF HESPERETIN GLYCOSIDES BY XANTHOMONAS CAMPESTRIS AND CYCLODEXTRIN GLUCANOTRANSFERASE AND THEIR ANTI-ALLERGIC ACTIVITIES" * |
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